Compound ID | 2100

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Streptomycin

Class: Aminoglycoside

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Inhibits protein synthesis by binding to the 30S subunit of the bacterial ribosome. Active against Gram-positive (incl. Mycobacterium tuberculosis) and Gram-negative bacteria
Description: Streptomyces natural compound; human use in tuberculosis in combination, used as pesticide; off-patent
Year first mentioned: 1944
Highest developmental phase: Approved by FDA in 1946
Development status: Approved
Reason Dropped: Other formulations were discontinued
Chemical structure(s):
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Molecular weight: 581.57
Iso. SMILES: C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(C=O)O
InChI Key: UCSJYZPVAKXKNQ-HZYVHMACSA-N
Can. SMILES: C[C@H]1[C@](C=O)([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@H](CO)O3)O)O)NC)O
InChI: InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/19649
Guide to Pharmacology: streptomycin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/36209173/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3290537/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8701281/
  • https://pubmed.ncbi.nlm.nih.gov/1882032/

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